A goal of bioorganic chemists is to develop a better understanding of biological processes by studying synthetic model systems. This proposal concerns such a study of ion channels. A series of potential ion channels has been designed which utilizes the basic interactions of steroids (cholesterol) with phospholipid bilayers. Specifically, the proposed macromolecules consists of six cholesterol analogs appended to an [18]crown-6 ether via amide linkages. The synthesis of these proposed ion channels is discussed in detail. The use of steroids and crown ethers should facilitate the preparation of a wide variety of possible ion channels since a large volume of literature has been devoted to both of these classes of molecules. The proposed potential ion channels will be incorporated into large unilamellar vesicles and their mediation of cation transport assessed by reported methods. Once a macromolecule that facilitates ion transport is found, systematic modifications will be carried out on this molecule to ascertain what the optimal location of heteroatom containing functional groups (binding sites) are for ion transport and how the rate of transport is affected by different functional groups.